How are the homes ordered?

Homes are shown from lowest to highest asking price within this page's price range.

Which Winter Garden addresses does this page cover?

The listings use the mapped Winter Garden city search area from our main guide. The selection does not cover every Winter Garden mailing address or every property in ZIP 34787.

Does the search include only detached houses?

No. It includes matching property types with at least one listed bedroom. Condos and townhomes can appear alongside detached homes. Review each listing's property type and ownership arrangements.

Does this budget search select a particular property type?

No. It retains the saved city boundary, asking prices below $300,000 and at least one listed bedroom. Check the property type and ownership details for each listing.

What should you compare beyond the purchase price?

Request information about recurring association charges, property upkeep and work you would want to complete. Build a property-specific comparison so a lower asking price does not obscure a different set of ongoing commitments.

What happens if there are no matching homes?

The page keeps its stated area and filters. It does not expand the search automatically. You can choose another budget or explore the wider Winter Garden guide.

Illustrative Central Florida home exterior with pale stucco walls, a covered entrance, a paved walkway and mature trees surrounding a landscaped lawn.

Homes for Sale Under $300K in Winter Garden FL

Browse Winter Garden homes asking less than $300,000. Compare current listings, layouts and ownership details within the mapped city area.

Homes for Sale Under $300K in Winter Garden FL

23 listings

3 days on market
$163,000
Bank owned (REO)
373 Eron Way Unit 47Winter Garden, FL, 34787
- 2 beds
- 2 baths
- 840 sqft
106 days on market
$188,000Price reduced by $11,999 on Oct 21, 2026
93 Windtree Lane Unit 102Winter Garden, FL, 34787
- 2 beds
- 2 baths
- 918 sqft
16 days on market
$189,000
87 Windtree Lane Unit KWinter Garden, FL, 34787
- 2 beds
- 2 baths
- 918 sqft
135 days on market
$199,999Price reduced by $15,001 on Sep 18, 2026
397 Eron Way Unit 42Winter Garden, FL, 34787
- 3 beds
- 2 baths
- 930 sqft
86 days on market
$199,999
844 Klondike StreetWinter Garden, FL, 34787
- 1 bed
- 1 bath
- 1,300 sqft
175 days on market
$204,900
170 Windtree LaneWinter Garden, FL, 34787
- 2 beds
- 2 baths
- 918 sqft
65 days on market
$204,900Price reduced by $7,100 on Sep 13, 2026
1315 Eastern Pecan Place Unit 202Winter Garden, FL, 34787
- 1 bed
- 1 bath
- 942 sqft
128 days on market
$214,000Price reduced by $10,000 on Aug 13, 2026
Short sale
359 Douglas Way Unit 54Winter Garden, FL, 34787
- 2 beds
- 2 baths
- 930 sqft
305 days on market
$218,000
92 Windtree Lane Unit 201Winter Garden, FL, 34787
- 2 beds
- 2 baths
- 918 sqft
58 days on market
$230,000
988 Stucki TerraceWinter Garden, FL, 34787
- 3 beds
- 3 baths
- 1,216 sqft
157 days on market
$239,000Price reduced by $3,000 on Oct 22, 2026
200 Southern Pecan Circle Unit 206Winter Garden, FL, 34787
- 2 beds
- 2 baths
- 1,276 sqft
80 days on market
$254,000Price increased by $30,000 on Oct 31, 2026
300 Eron Way Unit 1Winter Garden, FL, 34787
- 2 beds
- 2 baths
- 840 sqft
Browse all listings23 listings

View all matching homes

What this search includes

Current asking prices below $300,000, ordered from lowest to highest.

The selection uses the mapped Winter Garden city area and requires at least one listed bedroom. It can include condos, townhomes and detached homes. It does not cover every 34787 mailing address. Explore the full Winter Garden guide.

The hero image is illustrative; the listing cards show individual properties.

Begin with the rooms and responsibilities

Compare homes under $300K by the space you would use, the condition you would take on and the ownership arrangement. Measure furniture positions, check access and storage, and review recurring charges alongside the asking price.

Four checks for your Winter Garden shortlist

Usable rooms and storage
Check room dimensions, bedroom placement and storage against the way you plan to live.
Parking and daily routes
Check parking arrangements and test journeys from the exact address to your regular destinations.
Condition and upkeep
Review the property's condition and distinguish essential work from changes you would simply prefer.
Ownership commitments
Request the association information and compare recurring charges and maintenance responsibilities.

Separate essential work from optional changes

List what needs attention before moving in and what could wait. Request available information about the building or property and clarify maintenance responsibilities. A lower asking price does not establish a smaller commitment after purchase.

Compare the commitments for each address

Ask which parts of the property you would maintain and which are managed through an association. Request the relevant documents and clarify any separate charges or restrictions before choosing a home. The asking-price filter does not establish rental permission or amenity access.

Our Winter Garden HOA fees and ownership costs guide offers a useful place to continue your comparison.

Winter Garden citywide asking-price context

All prices, property types and bedroom counts in the saved city area. These are asking-price figures, not statistics for this selection.

For sale now: 194
Median asking price: $648,750

Questions about this Winter Garden search

Questions when comparing your shortlist

Gaby Sadler

Property Specialist, Serhant

Compare Winter Garden homes with Gaby

Tell me your priorities and your budget under $300K. I can arrange viewings and help you compare layouts, locations and ownership details across your Winter Garden shortlist.

+1 (407) 490-0475 realty@thetopvillas.com